Acetic Anhydride → HCID 86685411, compound

HRID 570753Notes

Reaction equation

HRID 570753 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][S:5][C:6]1[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:8](=[O:15])[C:9]2[C:10](=[CH:12][S:13][CH:14]=2)[N:11]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>O1CCCC1.CN(C)C1C=CN=CC=1>[O:15]=[C:8]1[N:7]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([F:26])([F:25])[F:27])=[CH:20][CH:21]=2)[C:6]([S:5][CH2:4][CH2:3][NH:2][C:35](=[O:37])[CH3:36])=[N:11][C:10]2=[CH:12][S:13][CH:14]=[C:9]12

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86685409HCID 86685409, compound

Product 1

HCID 86685411HCID 86685411, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-[(2-Aminoethyl)sulfanyl]-3-[4-(2,2,2-trifluoroethoxy)phenyl]thieno[3,4-d]pyrimidin-4(3H)-one hydrochloride (0.33 g) was suspended in tetrahydrofuran (30 ml), triethylamine (0.31 ml), acetic anhydride (0.28 ml) and 4-dimethylaminopyridine (37 mg) were added successively thereto, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The extract was washed successively with saturated aqueous citric acid solution, water and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained pale-yellow solid was purified by silica gel column chromatography (ethyl acetate/hexane) to give a colorless solid. This solid was recrystallized from ethyl acetate/hexane to give the title compound (0.22 g) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe extract was washed successively with saturated aqueous citric acid solution, water and saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained pale-yellow solid was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customto give a colorless solid
  8. customThis solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b2c4b6f7c8d143da8873e1446c38b8a2
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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